


Don't Shoot The Messenger

by destieldrabblesdaily



Category: Supernatural
Genre: First Kiss, High School AU, M/M, Misunderstandings
Language: English
Status: Completed
Published: 2016-01-14
Updated: 2016-01-14
Packaged: 2018-05-13 23:52:32
Rating: Teen And Up Audiences
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 2
Words: 2,865
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/5721763
Author URL: https://archiveofourown.org/users/destieldrabblesdaily/pseuds/destieldrabblesdaily
Summary: <blockquote class="userstuff">
              <p>Castiel's younger sister Anna wants to go to the school dance with Dean Winchester, but she doesn’t have the guts to ask him. Instead, she asks Cas if maybe he can do it for her and be the messenger. The tricky part? Castiel has feelings for Dean too.</p>
            </blockquote>





	1. Chapter 1

Castiel may or may not have been drooling over the sight of Dean Winchester. No, scratch that. Castiel Novak did _not_ drool, thank you very much… His thoughts however, were all over the place as he shamelessly stared at where Dean was standing by one of the lockers, surrounded by his group of friends. Dean’s perfect teeth showed when he threw back his head and laughed wholeheartedly at something that the blonde girl standing next to him had said. Dean’s laugh was the most precious thing in the world; his face glowing and his green eyes lighting up. Those eyes… Even though Castiel was watching him from the other end of the hallway, that endless maze of green took his breath away.

Alright, so perhaps Castiel was drooling a little. Not that he would ever admit it, not even to himself.

In other news, he couldn’t afford to get distracted right now. He had a mission, and as much as that mission made his stomach tighten painfully, he had promised his sister Anna that he’d do it.

An exasperated sigh sounded from beside Castiel, and a hand was lightly placed on his shoulder.

“I don’t mean to interrupt your ogling, Cassie… But are you honestly planning on being the messenger for your sister, even though you’re clearly head over heels in love with the guy  _yourself_?” A disapproving voice, laced with a heavy British accent, asked the question that Castiel himself had been struggling with all morning. “Because if you ask me, that sounds utterly ridiculous.”

Castiel’s best friend Balthazar was never one to beat around the bush, obviously. Whenever there was a room with an elephant in it that needed to be addressed, you could count on Balthazar to be the one to address it. And so, when Castiel had told him what he was about to do, Balthazar had made it no secret that he thought that it was a stupid idea.

“It is not ridiculous!” Castiel argued, rolling his eyes at his friend. “Anna likes him and wants to go to the Spring dance with him but she’s afraid to ask, and I’m helping her out because she’s my _sister_ and I care about her.” He explained patiently.

“And that would make all the sense in the world, if _you_ weren’t attracted to him as well.” Balthazar countered without missing a beat. “You have every right to pursue him yourself, you’ve been pining over the guy for months, and quite frankly, it’s about time for you to _do_ something about it.”

Castiel snorted humorlessly at that comment. If only things were that simple…

“For your information, as far as I know, Dean Winchester is as straight as they come.” Castiel said with a wistful glance at the beautiful boy with the freckled face. “There’s no point whatsoever in me going after him, so I might as well help out my sister.”

Balthazar was about to protest again, but they were both distracted when Castiel’s phone beeped in his pocket. He fished it out and checked his messages.

_‘Did you ask him yet? Did he say yes? I’m dying here, let me know when you talk to him! Anna’_

There was a skeptical click of the tongue from Balthazar who’d been reading along over Castiel’s shoulder.

“Good luck with that one, Cassie. When you start regretting this, I’ll be waiting for you with an ‘ _I told you so’_ like the great friend that I am.”

Castiel glowered at Balthazar who patted him on the back, then took off, leaving Castiel alone with his many doubts. Of course Balthazar was only trying to help him. Not to mention, he had made some very valid points, because this was going to be downright painful. The mere thought of Dean taking out Anna instead of him… But then again, if it wasn’t going to be Anna, it would be some _other_ random girl, so what difference would it make?

Castiel’s eyes were still fixed on Dean as the gorgeous Winchester boy gathered some of his books, then slammed his locker shut. Dean was bending over to put the books in his bag, and Castiel was treated to a very nice view of Dean’s ass, tightly hugged by dark jeans.

Swallowing the lump in his throat, Castiel tried to remove that image from his mind, instead focusing on the plan again. Admittedly, step one was already proving to be problematic; he’d have to try and get semi-popular Dean Winchester _alone._

~

Several hours later, and Castiel had tried _three times_ : In the cafeteria during lunch break, after English class where Dean only sat two desks away from him, and when passing Dean in the hallway between Spanish class and Biology class.

But Dean was never alone. Girls and boys alike were always swarming around him, and Castiel didn’t dare to walk up to him and talk to him, knowing that all of Dean’s friends would be watching their exchange.

During a free period, Castiel had basically given up for today. Instead he decided to go outside and get some fresh air as he waited for his last class to start. The weather was exceptionally nice for the time of year, and Castiel was sitting on one of the benches behind the school, soaking up some sun while he tried to catch up on his algebra homework.

“Do you mind if I sit here?”

A deep voice startled Castiel, and when he looked up from his notebook, he was met by a sea of _green_. Never before had Castiel seen that familiar shade of green from _this close_. The phrase _‘feeling butterflies in the stomach’_ suddenly made a lot more sense to him.

The one and only Dean Winchester was smiling down at him, and since Castiel had been stunned to silence, he nodded dumbly as a reply to Dean’s question.

“Great! The weather is way too nice to stay inside, huh?” Dean said nonchalantly as he flopped down onto the bench beside Castiel. “It’s Castiel, right?“

Castiel’s heart fluttered, and he knew then and there that nothing would _ever_ be as mesmerizing as the sound of his name rolling off of Dean’s tongue.

“I… Yes it is…” Castiel answered, finally capable to force out a few futile words.

Dean hummed and nodded. “Yeah, you’re in my English class.”

“I am.” Castiel muttered in confirmation, his hands restlessly fumbling with the pen that he was holding.

He was feeling extra nervous all of the sudden; By some miracle, Dean had ended up here on this bench with him, and _now_ was the time. If Castiel didn’t ask him now, he would probably not get another chance to help his sister get her much desired Spring Dance date…

“Look, Dean… Actually it’s good that you’re here, because I sort of need to ask you something…”

Every fiber of Castiel’s being was itching to look away from Dean’s radiant green eyes, but he knew it would be rude to have a conversation with someone without actually making eye-contact.

Dean seemed oblivious to Castiel’s uneasiness, and he smiled and tilted his head, hinting that Castiel could continue. Their bodies were angled towards each other now, and Castiel could feel Dean’s warmth even through his clothes.

“Alright… I’m not sure how I’m supposed to go about this, but Spring Dance is coming up and I…”

Before Castiel could even figure out for himself how he was going to complete that sentence, Dean already cut him off by smirking and placing a hand on Castiel’s knee, squeezing it gently.

“Thank God, dude! I thought you were _never_ going to ask! You were staring at me all day but you kept backing out, and I just _knew_ it had to be about this.”

Dean sounded almost… relieved. Castiel on the other hand, felt tremendously confused.

“I don’t understand, Dean.” He said slowly, glancing down briefly to see how Dean’s thumb started massaging circles into his knee, the simply action sending sparks through Castiel’s entire body.  

Dean shrugged. “I saw you, and I came out here to make it easier for you. Just saying though, I would’ve said yes anyway even when the others were around… I mean a pretty face like yours, and those big blues… Kinda hard to resist.”

Castiel’s mouth fell open when Dean’s declaration was followed by a suggestive eyebrow wiggle. And then Dean took the pen from Castiel’s hand, so that he could messily write down a number on Castiel’s notebook.

“I gotta go, Cas, or I’ll be late for class. But here’s my number, _text me_.” Dean said, handing the pen back to Castiel. “Maybe we can hang out this weekend, you know, talk about what time I’ll pick you up for the dance and stuff.”

Castiel opened his mouth to say something, but failed. The expression of raw shock on Castiel’s face apparently went unnoticed by Dean though; the green-eyed boy looked like he didn’t have a care in the world. He was about to get up from the bench, but then paused, grinning at Castiel as he dipped his head to swiftly kiss him on the cheek.

“See you later.” Dean breathed into Castiel’s ear before getting up and departing, a bounce in his step as he headed back to the building.

One of Castiel’s trembling hands touched the spot on his cheek where Dean’s lips had touched his skin, and he couldn’t help but smile goofily. This had gone wrong in all the right ways. Best. Misunderstanding. _Ever._

Once Castiel’s high wore off, he was certain of two things…

One: Dean Winchester was _not_ one hundred percent straight.

And two… Anna was probably going to _murder_ Castiel when he got home. Worth it.


	2. Chapter 2

Castiel knew that he should feel more guilty than he did. And sure, a part of him _was_ actually feeling quite bad about this… The problem was that it was difficult for Castiel to feel bad about anything at the moment, considering that he was currently slow dancing in Dean Winchester’s arms.

This had to be the best place on earth, the closest to heaven that anyone could ever get. Dean’s body was solid and warm against Castiel’s own, Dean’s hands lightly caressing Castiel’s back as they lazily swayed to the music together. Castiel’s chin was resting on Dean’s shoulder, and for now, Castiel had closed his eyes, reveling in the feeling of simply being here.

“You look pretty freaking amazing tonight, Cas.” Dean whispered in Castiel’s ear, effectively turning Castiel into a puddle of goo. “I could get used to seeing you in a suit.”

Castiel smiled against Dean’s shoulder at the compliment, glad that Dean at least wouldn’t be able to see him blush.

“You look quite stunning as well, Dean.” Castiel responded, meaning every word of it.

Dean hummed along to the music as they kept moving, neither of them paying any attention to the other couples on the dance floor because they were too caught up in their own little bubble. Castiel inhaled deeply, breathing in the sweet scent that was so typically Dean. Never in his life had Castiel felt _this_ content.

Regardless, that tiny voice in the back of Castiel’s head was persistently pointing out that this wouldn’t last… The second Anna arrived at the dance, she surely would be furious.

Needless to say, Castiel silently cursed himself for not telling her earlier. He’d wanted to,  _truly_ , but every time he’d been about to tell his sister the truth, he had chickened out. Instead he had lied to her, told her that Dean couldn’t go to the dance with her because he already had a date. Which okay, wasn’t a complete lie… The only detail Castiel hadn’t dared to mention, was that he _himself_ was Dean’s date.

After that, he had convinced Dean that there was no need for him to pick Castiel up for the dance, and that they would meet at the school instead.

And here they were, but although everything was perfect for now, Castiel was well aware that a confrontation with his sister was going to be inevitable tonight. She’d probably show up within now and…

“ _Castiel Novak_! I cannot believe you!” An infuriated voice stopped Castiel’s train of thought. A voice that belonged to his sister.

He felt Dean flinch in his arms at Anna’s sudden interruption, and Castiel reluctantly detached himself from a bewildered-looking Dean.

“Look Anna, I can explain, it was an accident…” Castiel put a hand on his sister’s arm to calm her down, but she was quick to swat it away.

“You stole my date!” Anna exclaimed, her eyes shooting fire. “Nothing about this is an accident!”

“Whoa whoa, what’s going on here? What the hell did I miss?” Dean asked, holding up both of his hands as his eyes flickered from Castiel, to Anna, then back to Castiel again.

“My brother is an asshole, that’s what you’ve missed.” Anna said, glaring at Castiel.

“You have to believe me, I had every intention of asking him to go to the dance with you, Anna.” Castiel pleaded with her. “Dean simply misunderstood and things… Went differently.”

“Well at least you could’ve told me the truth.” Anna hissed.

“I should have… And I truly _am_ sorry…” Castiel tried one last time, from the corner of his eye seeing how Dean’s entire face was tensing up.

“Of course you are.” Anna said sarcastically, rolling her eyes. “Save it, I’m going to enjoy myself with my friends, who at least aren’t complete douchebags! Have a _great_ night, brother!”

Castiel blinked and stared as Anna threw her vibrant red hair over her shoulder and stomped off. Once she was out of sight, he turned to look at Dean, who was looking shocked, but most of all, _hurt_.

“I’m sorry, Dean… I should’ve been honest with my sister, that way we could’ve avoided this… this _scene_.” Castiel apologized.

Dean frowned at him, eyes sad and uncertain. “You think I care about your sister causing a scene? That’s not what bothers me, Cas… I just… I thought you actually _wanted_ to go to the dance with me, but you’re only here because I jumped to the wrong conclusion, aren’t you?”

Castiel actually laughed out loud at how wrong that observation was.

“And now you’re _laughing_ at me?” Dean asked in disbelief.

They were still standing in the middle of the dance floor, and Castiel eyed the exit. “I want to clear this up, Dean… Can we go outside and talk?”

Dean nodded stiffly but complied, and Castiel let out a breath of relief. After a week full of lies, it was time for the truth, and nothing but the truth.

~

So Castiel and Dean had come full circle. They were sitting on the same bench where it had all started. It was chilly outside, but the sky was clear and the stars were bright. Castiel snuggled closer to Dean, chasing the other boy’s warmth. Dean’s arm slid around Castiel’s waist, pulling him in.

“So you _did_ wanna go with me, huh?” Dean murmured quietly, understanding, now that Castiel had finally given him the full story.

“I wanted it more than anything, Dean.” Castiel answered solemnly. “The only reason I helped out my sister was because I assumed that you weren’t interested in males, not in that way.”

“Hmm, well I’m not sure if I _am_ actually interested in males…” Dean mused.

Castiel stilled in Dean’s embrace at that admission, but before he could worry about it, Dean added “But I do know that I am interested in _you,_ Cas.”

Castiel peeked up to be met by Dean’s grinning face, and automatically he smiled back.

“Do you think your sister’s ever going to forgive you?” Dean asked conversationally while his fingers started to casually play with the strands of hair on the top of Castiel’s head.

Castiel grimaced at the reminder, his hands absently fumbling with Dean’s tie while he contemplated that. “I’m not sure… Anna is not usually one to hold grudges, but I think it would be best for tonight if I slept with one eye open, just to be safe.” He joked.

Dean snickered. “Yeah, she seemed pretty pissed…”

Castiel chuckled softly. “The last time I saw her _this_ angry was that day when our brother Gabriel gave her Barbie dolls a haircut, back when she was nine.”

They were both laughing now, and Castiel was once again reminded how lucky he was. Dean Winchester _liked_ him. When their laughter fell silent, they gazed at each other with dopey smiles on their faces.

“Oh well…” Dean muttered. “I’m not sorry things went the way they did.”

“Me neither…” Castiel confessed, falling deeper and deeper into those endless green eyes.

“Good.” Dean whispered.

And then Dean smirked mischievously, lowering his head ever so slowly and going in for a kiss.

As far as Castiel was concerned, all of his problems became insignificant the second their lips met. Dean’s lips were soft, and gentle, and so much better than any of Castiel’s fantasies. And if he was going to have to deal with his sister’s wrath during the next couple of weeks… Again, completely _worth it._

**Author's Note:**

> For more Destiel stories, go to destieldrabblesdaily.tumblr.com


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